Palladium-Catalyzed N-Monoarylation of Amidines and a One-Pot Synthesis of Quinazoline Derivatives
A method for the Pd-catalyzed N-arylation of both aryl and alkyl amidines with a wide range of aryl bromides, chlorides, and triflates is described. The reactions proceed in short reaction times and with excellent selectivity for monoarylation. A one-pot synthesis of quinazoline derivatives, via add...
| Main Authors: | , , |
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| Other Authors: | |
| Format: | Article |
| Language: | en_US |
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American Chemical Society (ACS)
2015
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| Online Access: | http://hdl.handle.net/1721.1/94324 https://orcid.org/0000-0003-3875-4775 |
| _version_ | 1826194812276047872 |
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| author | McGowan, Meredeth A. McAvoy, Camille Z. Buchwald, Stephen Leffler |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry McGowan, Meredeth A. McAvoy, Camille Z. Buchwald, Stephen Leffler |
| author_sort | McGowan, Meredeth A. |
| collection | MIT |
| description | A method for the Pd-catalyzed N-arylation of both aryl and alkyl amidines with a wide range of aryl bromides, chlorides, and triflates is described. The reactions proceed in short reaction times and with excellent selectivity for monoarylation. A one-pot synthesis of quinazoline derivatives, via addition of an aldehyde to the crude reaction mixture following Pd-catalyzed N-arylation, is also demonstrated. |
| first_indexed | 2024-09-23T10:02:11Z |
| format | Article |
| id | mit-1721.1/94324 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T10:02:11Z |
| publishDate | 2015 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/943242022-09-30T18:27:02Z Palladium-Catalyzed N-Monoarylation of Amidines and a One-Pot Synthesis of Quinazoline Derivatives McGowan, Meredeth A. McAvoy, Camille Z. Buchwald, Stephen Leffler Massachusetts Institute of Technology. Department of Chemistry Buchwald, Stephen Leffler McGowan, Meredeth A. McAvoy, Camille Z. A method for the Pd-catalyzed N-arylation of both aryl and alkyl amidines with a wide range of aryl bromides, chlorides, and triflates is described. The reactions proceed in short reaction times and with excellent selectivity for monoarylation. A one-pot synthesis of quinazoline derivatives, via addition of an aldehyde to the crude reaction mixture following Pd-catalyzed N-arylation, is also demonstrated. National Institutes of Health (U.S.) (Grant GM58160) National Institutes of Health (U.S.) (Postdoctoral Fellowship F32GM097771) 2015-02-11T15:56:25Z 2015-02-11T15:56:25Z 2012-07 2012-06 Article http://purl.org/eprint/type/JournalArticle 1523-7060 1523-7052 http://hdl.handle.net/1721.1/94324 McGowan, Meredeth A., Camille Z. McAvoy, and Stephen L. Buchwald. “Palladium-Catalyzed N-Monoarylation of Amidines and a One-Pot Synthesis of Quinazoline Derivatives.” Org. Lett. 14, no. 14 (July 20, 2012): 3800–3803. https://orcid.org/0000-0003-3875-4775 en_US http://dx.doi.org/10.1021/ol301700y Organic Letters Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use. application/pdf American Chemical Society (ACS) PMC |
| spellingShingle | McGowan, Meredeth A. McAvoy, Camille Z. Buchwald, Stephen Leffler Palladium-Catalyzed N-Monoarylation of Amidines and a One-Pot Synthesis of Quinazoline Derivatives |
| title | Palladium-Catalyzed N-Monoarylation of Amidines and a One-Pot Synthesis of Quinazoline Derivatives |
| title_full | Palladium-Catalyzed N-Monoarylation of Amidines and a One-Pot Synthesis of Quinazoline Derivatives |
| title_fullStr | Palladium-Catalyzed N-Monoarylation of Amidines and a One-Pot Synthesis of Quinazoline Derivatives |
| title_full_unstemmed | Palladium-Catalyzed N-Monoarylation of Amidines and a One-Pot Synthesis of Quinazoline Derivatives |
| title_short | Palladium-Catalyzed N-Monoarylation of Amidines and a One-Pot Synthesis of Quinazoline Derivatives |
| title_sort | palladium catalyzed n monoarylation of amidines and a one pot synthesis of quinazoline derivatives |
| url | http://hdl.handle.net/1721.1/94324 https://orcid.org/0000-0003-3875-4775 |
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